


Daddy Dean Drabbles - The Dress

by DandelionDreaming



Series: The Rookie Series [15]
Category: Supernatural
Genre: Boys can wear dresses, Brother chats and advice, F/M, Fluff and Humor, Gender Norms, LGBTQ Themes, Protective Dean Winchester, Sad Dean Winchester, Stereotypes, Unlearning Transphobia, Wise Sam, parenting
Language: English
Status: Completed
Published: 2020-11-17
Updated: 2020-11-17
Packaged: 2021-03-09 23:48:44
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,254
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27604454
Author URL: https://archiveofourown.org/users/DandelionDreaming/pseuds/DandelionDreaming
Summary: Because I couldn't leave them alone, I'm back with some Dean/Rookie snippets and drabbles set after 'If I Could See You One More Time'.Daddy Dean Drabbles is a G rated, sweet series about Dean navigating being a husband and father of twins - Charlie & Suzie. You're his wife, whom he calls 'his Rookie' because you got together when he was training you to be a hunter (seeThe Rookie Series).Note: Because I'm just writing little moments as I get inspired - the timeline is not linear/will jump around a bit, the twins age will always be written at end of the summary (and included somewhere in the story) as a guide.* * *Dean has messed up badly, so he video calls Sam to ask for help and advice on navigating gender norms for his son.Twins age 9 yrs old
Relationships: Dean Winchester & Sam Winchester, Dean Winchester/Original Female Character(s), Dean Winchester/You
Series: The Rookie Series [15]
Series URL: https://archiveofourown.org/series/1491710
Comments: 8
Kudos: 43





	Daddy Dean Drabbles - The Dress

**Author's Note:**

> Special mention to [Harry Styles making waves with his Vogue shoot](https://www.vogue.com/article/harry-styles-cover-december-2020) this week.

‘Hey Sammy, what’s up?’ Dean grinned into the camera. 

‘Dean? It’s still really early here.’ Husked Sam, stumbling out of his bedroom. The video feed from the phone giving Dean nothing but darkened hallway and ceiling as he made his way to the kitchen so he didn't wake the rest of the house.

‘Early bird catches the worm, rise and shine Sammy – rise and shine.’ Dean sang into the phone.

‘Crap. What have you done Dean?’ Asked Sam, rubbing his eyes and setting his phone on its stand in the kitchen as he began making himself a coffee.

‘What? Whaddya mean, what have I done?’ He sputtered. ‘Man can’t call his brother and say hello without having done something?’ 

‘No. Because I know you. And I know, you know, what time it is here.’ Sam yawned. ‘Also, you’re calling from the garage.’ 

‘I just thought you might be missing Baby is all. Look at her Sam, beautiful as ever hey.’ Dean smiled softly, turning back to look at the sleek lines of the ’67 impala. Maintaining her was becoming more and more labor intensive and expensive, but he still loved every minute. Suzie had taken to joining him in recent years, keen to know what the parts were called, excited to help him even if she was just passing him a wrench or sitting in her special 'watching and staying out of the way' spot. Her little nine year old face filling with joy when the engine turned over and the rumble started, eagerly scrambling to clamber inside and go for a ride.

‘The impala looks great, it’s nice to see her again. But if you’re out in the garage this early, it means you are either avoiding the house or you don’t want anyone to know you’re calling me... most especially your wife I’m guessing?’

‘Yeah, uh well. Rookie might be a little bent out of shape at the moment…’ Began Dean.

‘Because?’ Prompted Sam when the silence began to stretch.

‘It's not really my fault. I know it usually is, and I’m not proud of myself, but she shouldn’t have done it. She shouldn’t have let him do it. Or she should have at least talked to me about it first.’ Growled Dean.

‘Okay. So what should she have talked to you about?’ asked Sam patiently. 

‘I might have yelled at her for letting Charlie wear a dress to school.’ Mumbled Dean.

‘What? Why?’ Sam nearly burning his tongue on his coffee.

‘That's what I want to know - why would she let him wear the damn dress?! But I - uh, I was too busy yelling at her to find out. I didn’t even think he was into that stuff. Sure he’s not into cars and guns, and I didn’t care about the dolls thing when he was younger. But dresses at school? Jesus – what was she thinking?’ Grumbled Dean.

‘I meant why did you yell at her? Why didn’t you just ask her?’ Said Sam, shaking his head.

‘What? Oh. I don’t know. I was angry Sam, and all she said was ‘he wanted to’. I mean – he’s a nine year old boy. What the hell does he know about what he wants.’ Stuttered Dean.

‘You were handling a loaded gun, protecting me from monsters, cooking me meals and making sure I got to school when _You_ were nine Dean.’ Said Sam gently.

‘Exactly and look how messed up we turned out.’ He exclaimed.

‘So you asked her why, she said he wanted to.. then you lost it and told her she was wrong for letting him wear what he wants?’ Asked Sam, knowing there was more.

‘Yeah. Uh. M-Might have said that she was setting her kids up to be hurt. That people would call him weird and bully him. That he was sensitive enough without that crap and it was all on her.’ Dean said, looking down, his cheeks pink with shame. Sam knew him well enough to know the sudden furrowed concentration on his hands indicated just how embarrassed and sorry he was for what he’d said. And that he didn't know how to fix it.

‘And how did that go?’ Asked Sam, leaning back with a smirk.

‘I’m sitting in my garage calling you ain’t I? How do you think it went?’ Retorted Dean.

‘You didn’t say anything in front of Charlie – did you?’ Asked Sam, suddenly realising how much worse it would be if his nephew had heard.

‘No Sam. I’m a dick, but I’m not that much of a dick. I waited till he was in bed asleep.’ Dean muttered.

‘I poked the Mama Lioness and made her protective of her cubs. Never come for a woman’s children Sam, even if you didn’t mean it how it sounds, even if they’re yours too. She will rip you to shreds man. Not even blink - then, start all over again.’

‘That bad huh?’ Sympathized Sam, all the teasing gone.

‘She’s really mad at me Sam. Like - I don’t think I’ve ever seen her this mad. It's been three days and she won’t even look at me. Like she can’t look at me, because if she does she’ll rip me a new one all over again.’ He sighed.

‘So, what was the problem with Charlie wearing a dress Dean? Does he wear dresses often? Are you worried it’s because he’s gay?’ Asked Sam gently.

‘No Sam. No. I don’t care if he’s gay - You know that. I’d love him no matter what. It's just I’m worried about him being picked on, bullied. I want him to have friends and after school activities and all the good things. All the things we never had you know?’ 

He looked down at his hands and sighed.

‘I really want all the things for him Sam. I don’t want him to be sad, or scared, or hurt…’ He broke off, still not looking up at the screen. Sam waited a beat, knowing Dean wasn’t done. To expect an outburst, a channeling of his fear via anger. 

‘And shit, wearing dresses – why does he even want to wear a dress dude? He’s a boy. Boys don’t wear dresses. I mean what the hell man?’ He frowned, rubbing at his beard and standing up to pace in front of the screen.

‘You know they do right? Billy Porter wears dresses all the time… Tom Holland has dressed up. Since Harry Styles wore dresses for Vogue a few years ago, a load of guys have worn dresses - some in the LGBTQI community, some straight guys too. Its not a big deal anymore Dean.’

‘You’re gonna have to name names I actually know Sam.’ He growled.

‘Ok – how about David Bowie? Or that actor from that show you watch - Misha Collins? He wore a wedding dress to renew his wedding vows to his wife and she wore a tux.’ He countered. ‘And besides, you’ve taught both of them to look after themselves. I’m sure Charlie could handle a couple of bullies.'

Dean huffed out a breath, crossing his arms.

‘Yeah. I know they got it, but they’re nine years old Sammy – course I’m gonna worry. Hell, I still worry about you and you're a grown man.’ 

Did anyone actually say anything?’ Asked Sam.

‘Apparently it was only a couple of kids – their parents are douchebags so it ain’t exactly surprising. Charlie probably coulda handled it, but uh Suzie jumped in first.’ He looked over at the screen, unable to hold back his grin. ‘She’s such a firecracker. She reminds me of her Mom sometimes. She punched one of them in the nose and pushed the other one against the wall. Told him it’s not clothes that make a man, it's being kind, doing good and looking after people. Even horrible people like him.’ Dean chuckled. ‘Shit, I wish I’d seen it.’ 

‘Well, you know she’s right?’ Grinned Sam. ‘I mean come on Dean, You think the only reason we saved the world is because we were wearing jeans?’

Dean paused, looking up at him with raised eyebrows.

‘You’re too tall to rock a dress Sam, don’t be stupid.’ Dean's tone dismissive as he sat back down in the chair. ‘I on the other hand would probably look great in one. I’ve got the ass for it.’ He smirked, licking his lips. That trademark cheeky grin surfacing once more. 

‘Sure. You keep telling yourself that. Look, it sounds like Suzie and Charlie are all good – if they don’t care, then why do you?’

‘I don't know. Charlie is so freaking smart, even smarter than you were at his age. He wasn’t bothered at all, even talked the teacher out of giving them all detention if you can believe it. Said if it was bothering them, that it was for them to work out - not him. Outta the mouths of babes hey?’ Dean looked up, running his hand through his hair. ‘Think they got their wisdom from their Mom too.’

‘Think Rookie is gonna divorce you then? You know – if she’s so wise?’ Snorted Sam.

‘Don’t even joke man, I’m pretty sure she’s considered it a few times over the last few days. What do I say to her? ‘

‘Just tell her what you told me. That you got scared. That you were worried about Charlie, and you took it out on her because you didn’t know how to react or what else to do.’ Replied Sam.

‘Jesus Sam, you’ve been married a few years now, you must know you don’t just go round admitting that shit to your wife. I’ve only kept her this long by shutting up and not digging a deeper hole. If she finds out I’m that stupid, she’ll realise how stupid I am about everything and leave my dumb ass.’ 

‘Trust me Dean. She knows how stupid you are… and for some reason, she loves your dumb ass anyway. It won’t be news to her that you were scared and didn’t know how to react. What she needs to know - is that you know it, so that next time you’ll think twice.’ Sam looked at his brother, trying to be sure he was getting the message. 

‘What she really needs is to know that you’ll learn from this. That you’ll try harder next time, and most importantly that you won’t ever talk that way to Suzie and Charlie. I'm sure that’s what she’s most scared of, is that they might hear you and feel bad about themselves - because what their Dad thinks is everything to them. Remember how you were? You’d do anything for Dad’s approval... well - your kids are the same.’

‘Shit, surely she must know I’m nothing like my old man.’ Swore Dean. 'I mean I know I can be a bit of dick sometimes, but really?' He asked, rubbing his temple and staring at the picture he had on his workbench of his kids. Wondering if Charlie was scared of him, unaware how much Dean loved him and would do anything to make him happy. The thought making his stomach turn.

  
‘Yeah? How would Dad have taken to me wearing a dress?’ Laughed Sam, releasing the tension. Dean unable to help the bark of laughter that escaped his chest at the very thought of it. Both of them looking into the camera as the laughter died down, enjoying the brotherly moment, the weight and shared experience of being John Winchesters sons. Understanding the exchange without any further words needed. 

‘Yeah, I hear you. Okay.’ Dean nodded slowly. ‘So ‘fess up the fears’ you reckon? Crap. This marriage and parenting shit doesn’t get easier. Just you wait till your boys start wearing dresses.’ He sighed, shaking a finger at the screen.

‘I know. Don’t worry, if it helps any – this won’t be the last time you screw up… but seriously, you’re doing great Dean. Your kids are awesome and they love you a lot. So does your wife.’ Smiled Sam.

‘Thanks Sammy. Appreciate it.’ Dean stood slowly, leaning across the desk to shut down the laptop and end the call. ‘Guess I better go bite the bullet huh?’ 

‘You got this Dean.’

‘Thanks, bitch.’

‘Anytime… jerk.’ 

Still grinning as he shut down his phone, Sam looked around his still quiet kitchen and pondered how different their lives were. He wondered how many of the monsters and demons they’d taken down over the years would be horrified to know that the great Dean Winchester now fled from his wife in terror, and was more worried about mean school kids and playground bullies, than he’d ever been about ghosts and things that go bump in the night.

‘Sam?’ His head snapped up at the sound of his own wife’s voice coming from the bedroom.

‘You better be bringing me coffee after your brother called so god damn early.’ She replied.

‘Sorry babe. I’m on it.’ He called back, chuckling. Dean wasn’t the only one who didn’t like pissing off his wife.   
  
A few hours later his phone buzzed on the countertop.

Sam opened the picture message, nearly dropping his phone in surprise before he began to laugh. Dean stood next to Charlie in their living room, both of them wearing dresses.

_‘Figured this would be a good way to apologise to Rookie and hang out with Charlie. Make sure he knows his old man loves him, and has his back no matter what.'_

A second text followed shortly after.

 _'Have to say - it's kinda comfy. And I was right... my ass looks great_ 😁. '

FIN

**Author's Note:**

> Pix credit with thanks to the lovely Sandi ([via twitter](https://twitter.com/lemondropsonice)) for inspiration/use of the awesome snaps of Jensen & Baby in his garage during zoom panel last weekend.  
> * * *
> 
> Daddy Dean Drabbles is a G rated, sweet series about Dean navigating being a husband and fatherhood. You're his wife, whom he calls 'his Rookie' because you got together when he was training you to be a hunter.  
> You can read the (much more R rated) story - Hunter in Training via [The Rookie Series ](https://archiveofourown.org/series/1491710). Be warned - there is a lot of delicious smut. 🔥🔥🔥


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